NP-MRD: Showing NP-Card for 2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate (NP0219623)

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Record Information

Version

2.0

Created at

2022-09-05 20:40:56 UTC

Updated at

2022-09-05 20:40:56 UTC

NP-MRD ID

NP0219623

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

Description

2-O-Benzoyl-D-glucose belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. 2-O-Benzoyl-D-glucose is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-O-Benzoyl-D-glucose has been detected, but not quantified in, fruits. 2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate is found in Globularia nudicaulis. This could make 2-O-benzoyl-D-glucose a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    1.5737   -2.2657    0.5366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7971   -1.0483    0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -0.1816    0.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055   -0.5314    0.2663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3761    0.0366    1.4318 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5758    0.6088    2.3941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2907    0.9640    0.8777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3064    0.1789    0.3330 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5583    0.9790    0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5346    0.1455   -0.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455   -0.4195   -0.9381 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3903    0.1501   -2.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528   -0.2290   -1.0588 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9015    0.9928   -1.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627   -0.5203    0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2367   -1.3972    0.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5034   -0.8790    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7853    0.4678    0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    1.3067    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4198    0.8294    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367   -1.6384    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0167   -0.7169    1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4044    1.5372    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5817   -0.6588    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9652    1.3868    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3413    1.8348   -0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6409    0.4069   -1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9964   -1.5009   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1514   -0.4596   -2.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8965   -1.0085   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630    0.9549   -2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0349   -2.4631    0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3268   -1.5592    0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8112    0.8057    0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9337    2.3702    0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5891    1.5210    0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  4 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11  8  1  0
 20 15  1  0
 10 27  1  0
  9 25  1  0
  9 26  1  0
  8 24  1  1
  5 22  1  1
  6 23  1  0
  4 21  1  1
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 13 30  1  6
 14 31  1  0
 11 28  1  1
 12 29  1  0
M  END


  Mrv0541 05061307572D          

 20 21  0  0  0  0            999 V2000
    6.0340   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7485   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3196   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7485   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3196   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3196    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0340   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3196    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6051    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6051    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3196    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0340   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0340    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6051    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7485   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7485    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0340    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3196   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  1  0  0  0  0
 19  8  1  0  0  0  0
 19 13  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219623

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(O)C(OC(=O)C2=CC=CC=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O7/c14-6-8-9(15)10(16)11(13(18)19-8)20-12(17)7-4-2-1-3-5-7/h1-5,8-11,13-16,18H,6H2

> <INCHI_KEY>
RIDPBVGJGNVNFX-UHFFFAOYSA-N

> <FORMULA>
C13H16O7

> <MOLECULAR_WEIGHT>
284.2619

> <EXACT_MASS>
284.089602866

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.646620907898455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

> <ALOGPS_LOGP>
-0.77

> <JCHEM_LOGP>
-0.4372393693333334

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.775323355160879

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.301654565286315

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981079852836211

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
65.7454

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      11.263  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.597  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.930  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.597  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.930  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.930   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.263  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.930   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.596   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.596   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.930   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.263  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.263   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.596   6.160   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.262   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.262   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.597  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.597   0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      11.263   3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.930  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    8   14                                                       
CONECT    7    4    5   12                                                  
CONECT    8    6    9   19                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   13   20                                                  
CONECT   12    7   17   20                                                  
CONECT   13   11   18   19                                                  
CONECT   14    6                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19    8   13                                                       
CONECT   20   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoic acid	Generator

Chemical Formula

C₁₃H₁₆O₇

Average Mass

284.2619 Da

Monoisotopic Mass

284.08960 Da

IUPAC Name

2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

Traditional Name

2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(O)C(OC(=O)C2=CC=CC=C2)C(O)C1O

InChI Identifier

InChI=1S/C13H16O7/c14-6-8-9(15)10(16)11(13(18)19-8)20-12(17)7-4-2-1-3-5-7/h1-5,8-11,13-16,18H,6H2

InChI Key

RIDPBVGJGNVNFX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Globularia nudicaulis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Oxane
Benzenoid
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.77	ALOGPS
logP	-0.44	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.75 m³·mol⁻¹	ChemAxon
Polarizability	27.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034618

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013136

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14704603

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate (NP0219623)

MOL for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D MOL for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D SDF for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D-SDF for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

PDB for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D PDB for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

SMILES for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

INCHI for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

Structure for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)

3D Structure for NP0219623 (2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl benzoate)